Recent advances in transition metal-mediated trifluoromethylation reactions

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(75), P. 10442 - 10468

Published: Jan. 1, 2022

Fluorine compounds are known for their abundance in more than 20% of pharmaceutical and agrochemical products mainly due to the enhanced lipophilicity, metabolic stability pharmacokinetic properties organofluorides. Consequently, last decade has seen enormous growth incorporation a trifluoromethyl group into organic motifs. With significance, this review aims provide complete picture transition metal-mediated construction C(sp3, sp2, sp)-CF3 bonds via C-H/X bond functionalization or addition processes both aliphatic aromatic hydrocarbons. Diversified reagents ranging from radical electrophilic nucleophilic trifluoromethylating agents respective mechanisms have been further deliberated comprehensive overview. The coverage on topic is expected make unique beneficial future applications enriching community towards improvements field trifluoromethylation reactions, turn improving propensity development drugs.

Language: Английский

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Solvent-Dependent Selective Synthesis of CF₃-Tethered Indazole Derivatives Based on Multiple Bond Activations

Organic Letters, Journal Year: 2023, Volume and Issue: 25(5), P. 720 - 725

Published: Jan. 27, 2023

Presented herein is a solvent-dependent selective synthesis of CF3-tethered indazole derivatives via the cascade reactions 1-arylpyrazolidinones with trifluoromethyl ynones. Mechanistically, formation title products involves N–H/C–H/C–N/C–C bond cleavage along pyrazole ring and pyrazolidinone opening. For scaffold, 1-phenylpyrazolidinone acts as C2N2 synthon, while ynone serves C1 synthon. Meanwhile, also an enol unit to facilitate opening provide trifluoropropenoxy fragment alkynyl triple migration cleaved moiety. When reaction was run in trifluoroethanol instead DCE, it selectively afforded tethered trifluoroethoxy moiety through situ transesterification. To our knowledge, this first concurrent activation, formation, CF3 migration.

Language: Английский

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Synthesis of functionalized quinolines from the cascade reactions of N-aryl amidines with two CF₃-ynones via C–H/N–H/C–N/C–C bond cleavage

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1917 - 1923

Published: Jan. 1, 2024

We present a novel synthesis of CF 3 - and alkynyl-substituted quinoline derivatives based on Rh( iii )-catalyzed cascade reactions N -aryl amidines with two -ynones. Then, some products are transformed into polycyclic -benzo[ k ]phenanthridines through an intramolecular annulation reaction.

Language: Английский

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Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6246 - 6276

Published: Jan. 1, 2024

Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.

Language: Английский

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Vinyl azides in organic synthesis: an overview

RSC Advances, Journal Year: 2023, Volume and Issue: 13(2), P. 990 - 1018

Published: Jan. 1, 2023

This review focuses on the application of vinyl azide in organic synthesis and highlights new strategies methods using this compound to produce heterocycles other compounds.

Language: Английский

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Zn(II)-Catalyzed Multicomponent Sustainable Synthesis of Pyridines in Air

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3650 - 3665

Published: Feb. 28, 2023

Herein, we report a Zn(II)-catalyzed solvent-free sustainable synthesis of tri- and tetra-substituted pyridines using alcohols as the primary feedstock NH4OAc nitrogen source. Using well-defined air-stable Zn(II)-catalyst, 1a, featuring redox-active tridentate azo-aromatic pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (La), wide variety unsymmetrical 2,4,6-substituted were prepared by three-component coupling secondary with NH4OAc. Catalyst 1a is equally compatible four-component coupling. Unsymmetrical also via alcohol two different A series up to 67% yield 1-phenylpropan-1-one or 1,2-diphenylethan-1-one The 1a-catalyzed reactions proceeded efficiently upon replacing corresponding ketones, producing desired in higher yields shorter reaction time. few control experiments performed unveil mechanistic aspects, which indicates that active participation aryl-azo ligand during catalysis enables Zn(II)-complex act an efficient catalyst for present multicomponent reactions. Aerial oxygen acts oxidant dehydrogenation alcohols, H2O H2O2 byproducts.

Language: Английский

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Synthesis of CF₃-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7828 - 7842

Published: May 22, 2024

Presented herein is a novel synthesis of CF

Language: Английский

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Divergent synthesis of pyrrolizine derivatives through C−H bond functionalization of pyrroles

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(51), P. 6536 - 6539

Published: Jan. 1, 2024

Presented herein is the synthesis of diversely functionalized pyrrolizines from reaction

Language: Английский

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Synthesis of CF₃-Azafluorenes through the Cascade Reaction of 2H-Imidazoles with CF₃-Ynones

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

A concise synthesis of trifluoromethyl (CF

Language: Английский

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Novel Synthetic Method and Insecticidal Evaluation of CF₃-Containing Polycyclic Neonicotinoid Derivatives

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: 73(9), P. 5033 - 5041

Published: Feb. 22, 2025

The modification of active ingredients with a trifluoromethyl group represents significant approach for the discovery highly pesticides. Herein, we developed novel [3 + 3] annulation reaction neonicotinoid precursors and trifluoromethyl-α,β-ynones synthesized series CF3-containing polycyclic derivatives in high efficiency. insecticidal activity results indicated that most target compounds showed good activities against Aphis craccivora Nilaparvata lugens at concentration 100 mg/L. In particular, 3o 4k had LC50 values 1.53 1.47 mg/L A. craccivora, respectively, which were comparable to imidacloprid (LC50 = 1.30 mg/L). honeybee toxicity predictive model also potential low 4k. molecular docking study revealed exhibited favorable binding mode Lymnaea stagnalis acetylcholine-binding protein R55T-mutated resistant model.

Language: Английский

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